2-Acetylpyridine → 3-Hydroxy-1-isobutyl-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one
Reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:23])([CH2:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:6]1=[O:24])CCC.[CH2:25](N1C2C(=CC=CC=2)C(=O)C1=O)[CH:26](C)[CH3:27].C(C1C=CC=CN=1)(=O)C>>[OH:23][C:7]1([CH2:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([CH2:1][CH:26]([CH3:27])[CH3:25])[C:6]1=[O:24]Participants
4
Procedure
This compound was made in a similar manner to 1-butyl-3-hydroxy-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one using 1-isobutylindoline-2,3-dione and commercially available 2-acetyl pyridine (Fisher Scientific). 1H-NMR δ 8.70 (ddd, 1H), 8.13 (td, 1H), 7.92 (dd, 1H), 7.56 (ddd, 1H), 7.34-7.28 (m, 2H), 7.07-7.02 (m, 2H), 6.85 (d, 1H), 3.77 (d, 1H), 3.56-3.42 (m, 3H), 2.15 (m, 1H), 0.97 (dd, 6H). calculated mass for C19H20N2O3, 324.15. Observed, 325.1 (M+1).
Sources & evidence
- ORD record
- ord-509969f28b2d4ad0baf47c90a9116aeb
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079853B2
Reaction notes
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